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Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II

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Title: Jasmonic acid is not a biosynthetic intermediate to produce the pyrethrolone moiety in pyrethrin II
Authors: Matsui, Ryo Browse this author
Takiguchi, Kisumi Browse this author
Kuwata, Naoshige Browse this author
Oki, Katsunari Browse this author
Takahashi, Kosaku Browse this author
Matsuda, Kazuhiko Browse this author
Matsuura, Hideyuki Browse this author →KAKEN DB
Issue Date: 14-Apr-2020
Publisher: Nature Publishing Group
Journal Title: Scientific reports
Volume: 10
Issue: 1
Start Page: 6366
Publisher DOI: 10.1038/s41598-020-63026-3
Abstract: Pyrethrum (Tanacetumcinerariifolium) produces insecticidal compounds known as pyrethrins. Pyrethrins are esters; the acid moiety is either trans-chrysanthemic acid or pyrethric acid and the alcohol moiety of pyrethrins is either pyrethrolone, cinerolone, or jasmolone. It was generally accepted that cis-jasmone was biosynthetic intermediate to produce the alcohol moieties of pyrethrin, and the biosynthetic origin of the cis-jasmone was postulated to be jasmonic acid. However, there was no direct evidence to prove this hypothesis. In order to uncover the origin of pyrethrolone moiety in pyrethrin II, feeding experiments were performed employing deuterium- and C-13-labeled compounds as substrates, and the expected labeled compounds were analyzed using UPLC MS/MS system. It was found that the pyrethrolone moiety in pyrethrin II was derived from 12-oxo-phytodienoic acid (OPDA), iso-OPDA and cis-jasmone but not from methyl jasmonate and 3-oxo-2-(2 '-[Z]-pentenyl)-cyclopentane-1-hexanoic acid. The results supported that the biosynthesis of the pyrethrolone moiety in pyrethrin II partially used part of the jasmonic acid biosynthetic pathway, but not whole.
Rights: https://creativecommons.org/licenses/by/4.0/
Type: article
URI: http://hdl.handle.net/2115/79507
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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